Upcoming Events

There’s always something happening at Inn at Perry Cabin, and we invite you to be part of it. From waterfront gatherings and seasonal celebrations to relaxed moments that unfold throughout the day, our calendar brings people together in ways that feel easy, social, and genuinely enjoyable on Maryland’s Eastern Shore.

Settle in for open-air evenings like Summer Cinema on Linden Lawn, or step into experiences with a sense of occasion, from celebratory feasts to thoughtfully curated dinners. Holiday weekends bring their own energy, with Memorial Day, the Fourth of July, and Labor Day filling the property with outdoor events, live music, and moments that invite you to linger a little longer.

Whether you’re planning ahead or looking for things to do in St. Michaels, you’ll find a rhythm here that feels welcoming, lively, and worth saying yes to.

Winter

Chocolate bark food stand on Talbot Street in St. Michaels

8th Annual St. Michaels ChocolateFest

Indulge your sweet side at ChocolateFest on March 7, 2026! Sample decadent creations from local restaurants and shops, and explore the town while savoring chocolate-inspired delights.

Chesapeake Fire & Ice Festival in Easton

Just a 15-minute drive from St. Michaels in Easton, MD, the Fire & Ice Festival, February 20 & 21, 2026, dazzles with ice sculptures, live music, and seasonal festivities that warm the winter spirit.

Nordic SPA Experience

As a special Valentine’s experience, SPA at Perry Cabin introduces the outdoor Nordic Experience in partnership with Ritual Sauna & Plunge.

Rooted in warmth, release, and presence, this experience invites you to move between a wood-fired sauna and invigorating cold plunges, creating a deliberate contrast that refreshes both body and mind.

Offered in reserved time slots, the Nordic Experience may be enjoyed on its own or paired with SPA treatments, offering a thoughtful way to indulge this Valentine season. The experience is well suited for sharing, whether with a partner or close friends, and may be reserved for up to six guests.

Reserve through Guest Services by phone 443-258-2228 or email [email protected].

JOIN US SUPER BOWL LX

The game’s on, and we’re switching things up for the day. Brats, wings, smash burgers, pretzels, pitchers, and a few drink specials making a special appearance—plus raffle drawings at the end of each quarter. Super Bowl Sunday—less buttoned-up, more game-day.

Santa Claus lighting Christmas lights along the lane

Lighting of the Lane

Join us on Friday, November 28th for the beloved Lighting of the Lane, a cherished tradition that warmly welcomes the holiday season. Guests of the Inn are invited to step into a winter wonderland where snowflakes dance, Santa spreads cheer, and cozy beverages are enjoyed as we count down to the grand unveiling of lights along the lane.

Midnight Madness

Step into the magic of Midnight Madness the first weekend of December in St. Michaels. Our charming shops extend their hours, welcoming you with festive refreshments, delectable snacks, and exclusive sales. Every purchase at participating businesses brings you closer to winning delightful gift baskets, adding to the joy of the season.

Christmas in St. Michaels

Experience the magic of Christmas in St. Michaels from December 12 - 14! Join us for a weekend filled with joyous celebrations as our picturesque town comes alive with holiday spirit. Don't miss the enchanting Talbot Street Christmas Parade and the dazzling Lighted Boat Parade, where the waterfront sparkles with festive cheer. Throughout the town, discover a plethora of merry festivities to delight in with loved ones amidst the festive atmosphere of Christmas in St. Michaels.

Spring

Horticulturist Kyle Mitchell tending to garden boxes on the terrace

Enjoy a Garden Tour

Join us on Wednesdays and Sundays at 10:30 AM for a guided, horticulturist-led tour designed to share insight into our gardens, seasonal plantings, and landscape design. Learn what’s in bloom, how it’s cared for, and what makes each season unique. Reservations are recommended, as select dates may be unavailable. Call Guest Services at 443-258-2228 or email [email protected].

Discover Seasonal Garden Highlights

Tours are open to both Inn guests and day visitors, with pricing at $25 per person for non-hotel guests.

Summer Cinema on Linden Lawn

Beginning May 19, join us for complimentary open-air movie nights on Linden Lawn on select summer evenings, with films beginning at 8 PM. Bring a blanket or lawn chair, settle in under the stars, and enjoy movie-style concessions with a Perry Cabin twist available for purchase. In the event of rain, screenings will be held the following evening.

*Films subject to change based on licensing.

Return of the Fleet

On Saturday, April 11 from 1:00 - 4:00 PM, join us for our most anticipated celebration of the year complete with live music by Justin Ryan throughout the afternoon!

Admission is $25 per person and includes complimentary Veuve Clicquot and fresh shucked Oysters from 2:00–3:30 PM.

At 2:30 PM, the fleet arrives to the sound of bagpipes, marking the return of the season, followed by remarks from Captain Jason and the traditional Blessing of the Fleet.

A cash bar and light bites will be available throughout the afternoon as the music continues until 4:00 PM.

RSVP encouraged as space is limited, 443-258-2228 or [email protected]. Tickets purchased at door.

St. Michaels WineFest

Sip and explore a wide range of international wines during the Wine Tasting Festival, taking place Saturday, April 25 – Sunday, April 26, 2026. Featuring vineyards from renowned wine regions around the world, the event offers a relaxed way to discover new favorites and enjoy a spring weekend.

Easter on the Miles

In addition to pony rides and the petting zoo, the Easter festivities continue with a festive Easter Egg Hunt at 11:00 AM, available exclusively for brunch guests and guests of the Inn. Then, enjoy Easter Day Dining with seatings from 12:00–4:30 PM, and keep an eye out for a very special guest — the Easter Bunny will be hopping around throughout the day, ready for photos, smiles, and a touch of springtime magic.

For dining details, please visit our dining page.

Cinco de Mayo in Purser’s Pub

Tacos, tequila, and a reason to celebrate—Cinco de Mayo in Purser’s Pub has all the right ingredients. Starting at 2 PM, enjoy Chef Elmer’s festive features and a rotating lineup of handcrafted margaritas designed for sipping the afternoon (and evening) away.

cinco de mayo SPECIALS

Talbot Humane Paws & Plates

Rain, Rain, Go Away… We’re Paws-ing ‘til a Brighter Day! Due to the forecast, Paws & Plates has been rescheduled to Wednesday, June 18. Same location, same pup-approved fun!

Join us for Paws & Plates, a dog-friendly evening at the Lighthouse on the Pointe, welcoming locals and visitors alike from 4 to 7 pm. Bring your pup and enjoy live music, our pizza oven, and a wine and beer bar, all while supporting a great cause: 10% of proceeds will benefit Talbot Humane Society. Don’t miss the doggie menu and pop-up shop filled with treats and toys for your four-legged friend!

Sparkling Afternoons

Slide into the spirit of summer with us on Fridays, June 13, and 27, and Saturday, June 21, from 3–6 PM. Partake in sun-drenched afternoons with live music, sweeping waterfront views, tasty bites, and crisp, refreshing beverages. The carefree rhythm of summer starts now!

Easter Day Petting Zoo & Pony Rides

Pony rides, a petting zoo, and a very hoppy visitor bring Easter day joy for the whole family. Join us on Linden Lawn from 9:00–11:00 AM as Wild Kid Acres Farm arrives with a mini cow, donkey, pig, goat, chicken, and turkey for up-close springtime fun. Admission is $20 per person, with pony rides available for $15 for one ride or $25 for two rides.

Market stall with people browsing colorful glass bottles and stones.

Eastern Shore Sea Glass and Coastal Arts Festival

Save the date for the upcoming Eastern Shore Sea Glass and Coastal Arts Festival, taking place Saturday, April 18 and Sunday, April 19, 2026 at the Chesapeake Bay Maritime Museum in St. Michaels, Maryland. This Spring Edition promises an extraordinary showcase of coastal craftsmanship, with over 90 exhibitors presenting a diverse collection of jewelry, home décor, art, and more.

Mom and her little ones on a boat charter

Mother's Day

Bring Mom for a day that’s easy, a little indulgent, and meant to be enjoyed together. Start with a relaxed brunch, linger over a second mimosa, then wander the gardens or settle in by the water. No schedule, no pressure, just good food, fresh air, and time well spent.

Mother’s Day Dining Menu

Summer

Moments in Time

Tuesdays in June & July beginning June 2 at 10:30 AM
Enjoy a guided journey through the rich history of St. Michaels, from colonial life and Frederick Douglass to shipbuilding traditions and the War of 1812, concluding with lunch on Samuel Hambleton’s waterfront terrace overlooking the Miles River and the historic battlefield where the town famously fooled the British.

Tour & Lunch | $80 per person | Includes a $5 contribution to the Talbot County Historical Society.
Tax and gratuity are additional.
Reservations details coming soon...

Sails & Salutes: A 250th Boat Parade Celebration

Sunday, June 14 • The Pointe • 12–4 PM
Ticket Pricing & More Details Coming Soon...
Join us for an afternoon of waterfront festivities during the St. Michaels Flag Day Boat Parade. Gather on the lawn at The Pointe for front-row parade views, live music, lawn games, nautical activities, and Chesapeake-inspired fare.

CBMM Antique & Classic Boat Festival and Coastal Arts Fair

Plan ahead for the 38th Antique & Classic Boat Festival at the Chesapeake Bay Maritime Museum, happening Friday-Sunday, June 19-21! Enhance your experience with a stay at Inn at Perry Cabin for the ultimate Chesapeake retreat. Visit here for event details and highlights.

Founding Father's Feast

Wednesday, July 1st

Powdered wigs optional — appetite required.

Inspired by the entertaining traditions of early America, Founding Father’s Feast invites guests on a culinary journey through colonial times for the original farm-to-table experience. This five-course tasting menu is curated through the lens of George Washington, Alexander Hamilton, John Adams, Thomas Jefferson, James Madison, and Benjamin Franklin’s favorite foods and drinks.

The evening begins with a reception at The Pointe before moving into the Commodore Ballroom for a spirited dinner filled with historic flair, period-inspired touches, and plenty of storytelling along the way.

Reception | 6:30 PM
Dinner | 7:30 PM
$177.60 per person, includes tax and gratuity.
Reservation details coming soon...

Fourth of July Weekend

Ticket Pricing & More Details Coming Soon...
Celebrate Independence Day and 250 years of American spirit along the Miles River with live music, festive waterfront gatherings, seasonal cocktails, and elevated summer fare at Inn at Perry Cabin.

Friday, July 3
3–6 PM | Live Acoustic Strings
Waterfront Terrace
Veuve Clicquot, Rosé & Sancerre
Harris Creek Oysters with Pickled Watermelon & Garden Mint Relish

Saturday, July 4
12–3 PM | D.J.
The Pointe
Upscale Crush Bar, Beer & Wine
Wood-Fired Pizza & Roasted Summer Bites

Sunday, July 5
12–3 PM | Live Bluegrass Music
The Pointe
Red, White & Blue Cocktails, Beer & Wine
Eastern Shore BBQ Featuring Slow-Roasted Chicken, Smoked Pulled Pork & BBQ Shrimp

St. Michaels Fireworks Sail

On Sunday, July 5 from 8 - 10PM, step aboard for an evening sail on the Miles River timed with the St. Michaels fireworks display. Cruise along the Miles River at sunset before settling in for views of the fireworks from the water with bubbly and sweet treats served aboard.

Pricing and more details coming soon...

Plein Air Easton

Plein Air Easton, celebrating its 22nd year July 10 - 19, 2026, is the largest juried plein air painting competition in the U.S and a perfect excuse to plan a visit. Hosted by the Avalon Foundation in Easton, Maryland, each July, it draws talented artists from around the world.

CBMM Watermen’s Appreciation Day & Crab Feast

Mark your calendars for Sunday, August 9th as the Chesapeake Bay Maritime Museum comes to life with the Waterman’s Appreciation Day & Crab Feast. Pair these nautical spectacles with a stay at Inn at Perry Cabin for the ultimate Chesapeake retreat! Visit here to read about the history and importance of the Chesapeake Bay Watermen.

Couple relaxing in Adirondack's on the Manor Lawn